6A,6C-hexakis(2,3-di-O-methyl)-α-cyclodextrin | 147238-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6A,6C-hexakis(2,3-di-O-methyl)-α-cyclodextrin
• 英文别名: 6^A,6^C-hexakis(2,3-di-O-methyl)-α-cyclodextrin
• CAS: 147238-00-4
• 化学式: C₆₆H₁₀₀O₃₂
• 分子量: 1405.5
• InChiKey: GLOWPRWJIROKEX-DSFYVVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  98.0
• 可旋转键数：
  28.0
• 环数：
  24.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  339.36
• 氢给体数：
  4.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  6A,6C-hexakis(2,3-di-O-methyl)-α-cyclodextrin 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到6^A,6^C--6^B,6^D,6^E,6^F-tetra-O-methylhexakis(2,3-di-O-methyl)-α-cyclodextrin
  参考文献：
  名称：

  Novel cyclodextrin-oligosiloxane copolymers for use as stationary phases to separate enantiomers in open tubular column supercritical fluid chromatography

  摘要：

  Five novel beta- (or alpha-) cyclodextrin- hexasiloxane copolymers have been prepared by a seven- (or nine-) step process. A key step was the reaction of partially alkylated beta- (or alpha-) cyclodextrin (8, 9, or 10) with p,p'-methylenebis(benzenesulfonyl chloride) to form a bissulfonate ester on the smaller rim of cyclodextrin. These bissulfonates were reacted with sodium p-(allyloxy)phenoxide followed by alkylation to form the peralkylated bis(allyloxyphenyl) beta- (or alpha-) cyclodextrins 17-20. Beta-Cyclodextrin bissulfonate ester 11 was also reacted with sodium azide followed by methylation, reduction, and acylation to form permethylated N,N'-bis[(allyloxy)benzoyl]-6A,6C-diamino-6A,6C-dideoxy-beta-cyclodextrin (24). The bisalkenes were copolymerized with dodecamethylhexasiloxane by the hydrosilylation process to give the cyclodextrin-containing copolymers. The copolymeric phases provided excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC).

  DOI：

  10.1021/jo00061a035
• 作为产物：
  描述：

  per(2,3-di-O-methyl)-α-cyclodextrin 在 吡啶 、 sodium hydride 作用下， 反应 27.5h， 生成 6A,6C-hexakis(2,3-di-O-methyl)-α-cyclodextrin
  参考文献：
  名称：

  Novel cyclodextrin-oligosiloxane copolymers for use as stationary phases to separate enantiomers in open tubular column supercritical fluid chromatography

  摘要：

  Five novel beta- (or alpha-) cyclodextrin- hexasiloxane copolymers have been prepared by a seven- (or nine-) step process. A key step was the reaction of partially alkylated beta- (or alpha-) cyclodextrin (8, 9, or 10) with p,p'-methylenebis(benzenesulfonyl chloride) to form a bissulfonate ester on the smaller rim of cyclodextrin. These bissulfonates were reacted with sodium p-(allyloxy)phenoxide followed by alkylation to form the peralkylated bis(allyloxyphenyl) beta- (or alpha-) cyclodextrins 17-20. Beta-Cyclodextrin bissulfonate ester 11 was also reacted with sodium azide followed by methylation, reduction, and acylation to form permethylated N,N'-bis[(allyloxy)benzoyl]-6A,6C-diamino-6A,6C-dideoxy-beta-cyclodextrin (24). The bisalkenes were copolymerized with dodecamethylhexasiloxane by the hydrosilylation process to give the cyclodextrin-containing copolymers. The copolymeric phases provided excellent enantiomeric separation of a variety of chiral solutes in open tubular column supercritical fluid chromatography (SFC).

  DOI：

  10.1021/jo00061a035